


In the Air Tonight

by Captain_Loki



Category: Teen Wolf (TV)
Genre: Bottom Stiles Stilinski, First Time, Humor, M/M, Oral Sex, Rimming, Sexual Humor, sexual discussion
Language: English
Status: Completed
Published: 2013-05-06
Updated: 2013-05-06
Packaged: 2017-12-10 15:04:30
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,760
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/787379
Author URL: https://archiveofourown.org/users/Captain_Loki/pseuds/Captain_Loki
Summary: <blockquote class="userstuff">
              <p>Derek has never been with a guy before, thankfully Stiles has a lot of theoretical knowledge and a thirst for experimentation, he's a veritable Gay Yoda, Gayda if you will, except probably don't use that word actually.</p>
            </blockquote>





	In the Air Tonight

**Author's Note:**

> Warning for mentions of past kate
> 
> based on a [tumblr prompt](http://captain-snark.tumblr.com/post/49801368244/in-the-air-tonight-sterek-fic)

They get together just after Stiles’ eighteenth birthday, like right after, like the day after. They’re friends now, which is nice, and so it’s not even weird or awkward when Derek asks Stiles what he wants for his birthday. Stiles has plans, it’s the big One Eight, the year of official adulthood, you know _legal_ , though he doesn’t actually mention this directly to Derek because Stiles is all about the subtlety. So, instead he just sort of smiles and says, “I want to go to the movies.”

Derek doesn’t actually question this, he does raise his eyebrow slightly dubiously even as he nods his agreement. So, Derek takes Stiles to see the newest Marvel movie and then afterwards they go out for dinner. It’s not super special or anything, except for how it kind of is, and Derek tries to embarrass Stiles by telling their waitress it’s his birthday and they bring out a cake and sing a ridiculous song and the whole restaurant stares as Derek laughs at him, and Stiles feels his face heat from something more than his total humiliation.

And then afterwards they end up at this laser tag place that’s open until like three in the morning and play laser tag all night with a bunch of drunk college students, and it’s probably the best birthday Stiles can ever remember having, definitely the best since his mom died, and he’s never seen Derek smile so much without grit and sarcasm fueling it.

When Derek drives Stiles home, it’s like two in the morning and he’d be breaking curfew if he had it but he’s eighteen, and anyway he’s pretty sure his Dad knows what tonight’s about even if Derek doesn’t. So, Stiles sort of smiles softly at Derek when he throws the car into park in front of Stiles’ drive and looks over at him.

“You know this was a date, right?” Stiles asks, just to make sure. This sort of shy kind of exasperated grin crosses Derek’s face and he lets out a soft breath of laughter and nods. “I had sort of deduced, Stiles,” he says. Stiles beams at him from the other side of the car and leans forward, kisses Derek quick and chaste before sitting back in his seat.

“Good, because like the date was sort of just the packaging,” Stiles tells him, and Derek quirks a brow. “You know, cos what I really wanted for my birthday was you?” Stiles clarifies and Derek actually sort of flushes then, but Stiles isn’t totally sure because it’s pretty dark, but he’s calling it a win.

“I know,” Derek tells him.

“So, can we like…you know…date? Like on the regular?” Stiles asks. And then Derek is nodding and kissing him again. And that’s pretty much how it starts.

It’s been three months, and Stiles had been pretty sure having a steady boyfriend would have meant getting the D; at least like sneaking a quick peek at the D or talking about the D, whispering sweet nothings to the D after sucking it into willful submission.

Mostly, his relationship involves a lot of kissing and heavy petting, flitting somewhere in between second and third base. Stiles has almost come in his pants more times than he can count, though he does have to admit it’s still pretty awesome when he can feel Derek nearly do the same beneath him, but still.

And they hadn’t really had a discussion about it but Stiles had made the sweeping assumption that Derek just wanted to wait, you know, for Stiles to like…not be an awkward teenager or something. Which, Stiles is fairly certain will never happen. Sure, in two years he’ll be twenty but he doesn’t think his personality is a passing phase.

He has to throw all of his terrible misconceptions out of the window when Derek says to him one evening, as Stiles’ fingers start tugging at his belt and he makes it known he’s totally ready for this, that “I’m not.”

“Oh.” Stiles sits back on the bed, and feels his dick sort of wilt under that particular confession. “Is it me?”

“What? No,” Derek shakes his head but Stiles can see him getting all quiet and cagey the way he does sometimes when he has to talk about things like _feelings._ And then it turns out that Stiles’ whole worldview has shifted because Derek is _not_ the Casanova he’d thought.

“Casanova, Stiles?” He laughs, “really?”

“Umm, I’m sorry aviators and leather clad swag, what was I supposed to think?” Stiles asks a little huffy. “Have you seriously only ever been with two people?”

“Yeah,” he admits.

“Well you do know I’ve been with a total of no people. None peoples, Derek, I literally have no basis of comparison here,” Stiles tries to reassure him. And then Derek gets all fidgety and starts pacing and that’s never a good sign and Stiles suddenly thinks he knows what’s going on, because he knows Derek, he knows how much he hates going into a situation without all the answers.

“You’ve never been with a dude?” Stiles guesses.

“No,” Derek admits.

“So, you’ve got a clean buttsex slate, I can work with that,” Stiles tells him.

“Oh my God,” and then Derek is collapsing back against Stiles’ bed and covering his face with his hands, not looking at him. Stiles smirks at him, because _Stiles_? Stiles is good at this part, he has some serious theoretical knowledge to work with here.

But then Derek is telling him other things, things that aren’t so happy and with the sexy making, things about Kate Argent and, “wow, I need to go find Peter,” Stiles him then and Derek gives him this sort of confused alarmed look, “he’s the only one I know who has experience coming back from the dead, and I’d really like to kill Kate Argent myself,” Stiles explains. And Derek gets this soft sort of sappy expression on his face like no one has ever offered to do something like that for him before, and Stiles just wants to kiss his face and keep him forever. Which Stiles is pretty much hell bent on doing, actually, and says so.

After that Stiles decides to take matters into his own hands, in order to take matters into everyone’s hands and butts, if he can swing it. And the thing is, Stiles’ is pretty sure Derek is all self-conscious about the whole thing because he’s supposed to be the adult, and he’s spent the better part of their relationship pretending like he knows way more than he lets on, and he’s “twenty five and didn’t have any idea what the hell the prostate could be used for.”

But the thing of it is? Stiles finds it unspeakably hot. Literally, he tries to explain to Derek how much of a boner popper it is, but can’t because his vocabulary is shot to shit in the face of Derek Hale flushing to the tips of his ears when Stiles bandies about words like ‘butt plug’ and ‘cock ring’.

“So, my complete lack of experience is sexy?” Derek asks, skeptically. Stiles is sitting astride his lap, kissing his way up Derek’s neck and grinning.

“No, the fact that you’re willing to share that experience and inexperience with me is sexy,” Stiles clarifies. “I was worried I would have no idea what to do and you’d be like this…sex guru,” Derek raises his eyebrows in serious judgment. Stiles flushes and scowls. “But you have no idea what you’re doing so it’s all good.”

“It’s perfect,” Derek rolls his eyes.

“It is,” Stiles agrees, ignoring his sarcastic tone, “you’re perfect,” he laughs, “you are, c’mon, I love you.” He confesses, and he’s pretty sure it should sound bigger or something, but mostly it sounds small and sincere and he finds he really means it.

“Stiles,” Derek starts and Stiles presses his finger to Derek’s mouth.

“Hey, I’m not saying I’m in love with you or anything, and I’m not saying I’m not either, for the record, I’m just saying I care about you. And like, I do.” Derek pauses for a moment and kisses Stiles’ finger, “I love you too.”

 

So, Stiles figures if he’s going to get this right he has to do this right, right? So, he prints out a big honkin list of sex things (it says it right there at the top of the page in comic sans because Stiles is nothing if not hilarious: 

 

“What the ever loving hell is this?” Derek asks him when Stiles flourishes it in his direction with an uncontrollable smile.

“Just…highlight all of the things you’re interested in with the blue,” Stiles tells him, handing him a couple of highlighters, “and highlight all the things that could be triggering in yellow,” he explains.

“Stiles…I don’t even know what half of these things are?” Derek says, and his eyes widen as he scans the page. He looks at Stiles forlornly so Stiles sits Derek down on his bed and hands him his tablet, urbandictionary all cued up because Stiles comes _prepared_.

Derek is still looking a bit skeptical but he does as he’s told, and Stiles starts highlighting his own list for comparison later. There’s mostly comfortable silence then, punctuated occasionally by noises from Derek’s side of the room. A casual sort of ‘hmming’ or a soft gasp of surprise, every once in a while an outraged “why would anyone _want_ that?!” 

They have a conversation about kinks and safe spaces and the fact that Stiles is 100% judgment free; but it turns out Derek’s list of blues is (unsurprisingly) small, and there are several things highlighted in yellow that Stiles gets.

“Can I uh…see yours?” Derek asks and Stiles hands his own sheet over with a sly sort of grin. Derek’s face gets more and more flushed as he scans the page. Eventually, he looks up, clears his throat a little and says “I uh…didn’t put…on mine cos I wasn’t sure if…” he _stutters_ and Stiles wants to brain himself on the corner of his desk he’s so cute but he doesn’t think Derek would appreciate the sentiment.

“What?” Stiles asks instead, “what’d you want to try?”

Derek clears his throat again and doesn’t look at him, “rimming?”

 

After that Stiles goes on a porn collecting spree (mostly this involves bringing out the old external porn drive and plugging her in), but he grabs links and clips and vids from various scenes, a whole range from filth to vanilla to fingering to DP.

“I have a sort of…experiment I guess,” Stiles starts that evening at dinner. “If you’re game?” He asks. Derek looks up from the spaghetti he’s prepared and looks at Stiles with slight trepidation.

“You can say no,” Stiles assures him, “I just thought it might make talking about what you might want easier?”

“How so?” Derek asks, interested.

“By, well, _not_ talking about it,” Stiles offers by way of explanation. Because he knows Derek isn’t very good at voicing things aloud, he always feels too overwhelmed by his own thoughts to articulate them the way he wants and he’s much better at showing than telling anyway.

“Do you trust me?” Stiles asks, and for a minute he’s genuinely unsure of the answer, until Derek is looking at him across the table and there’s a line of tension that leaves his shoulders and he’s nodding, “yes, I do.”

So, after dinner Stiles helps clean the dishes and they watch an hour of television Derek has queued up on the DVR and then Stiles is pulling out his laptop, setting it up on the coffee table in front of them. He untangles the cords from his backpack and goes about hooking the computer up to Derek’s tv monitor as Derek watches with silent, rapt attention.

“I uh…have some stuff I wanted to maybe watch?” Stiles explains, and Derek seems to get it then. He flushes up his cheeks, the back of his neck reddening. “Is that okay?” Stiles asks and Derek nods, “yeah.”

“Okay, cool. I thought…maybe if you wanted, you know if it was okay we could do it like…” Stiles hesitates, and then he just sighs out his uncertainty and starts unbuttoning his pants, kicking off his shoes and watching Derek for signs of disapproval. Derek doesn’t offer any and Stiles steps out of his pants and moves over to the couch in his t-shirt and boxer briefs.

Derek also doesn’t protest when Stiles starts pulling his pants off, undoing the button and pulling down the zip on his fly and tugging them carefully down his thighs then calves and off, already barefoot. Stiles grabs the remote out of his backpack. Derek sits up a little in his seat as Stiles turns around in front of him, lowers himself carefully into Derek’s lap as he just stares up at Stiles with this look of open fascination on his face.

“I thought if we did it like this,” Stiles explains, settling himself against Derek, “neither of us would really have to talk about what was a turn on we’d just be able to…you know…tell?” Stiles says, uncertain. “You’re sort of working with a supernatural advantage, here,” he laughs. Stiles isn’t even sure Derek is paying attention to him, his hands are spanning across Stiles’ hips and he’s nosing at the middle of Stiles’ back.

“I don’t know if this is going to work,” Derek admits.

“Oh?”

“Yeah, it doesn’t matter what the hell you play Stiles,” he explains, “you in my lap in your underwear pretty much does it for me,” he finishes. Stiles laughs against him, and _whoa yup_ , there it is, Derek’s cock growing hard beneath him, twitching against his ass, Stiles’ own stirring awake.

“Did you want to watch, though?” Stiles asks and Derek nods, wraps himself around Stiles a bit more as Stiles opens up his porn folder and clicks on a thumbnail. It turns out, it really doesn’t take that much time before they’re both hard and leaking into their respective shorts, Stiles’ hips starting to grind down against Derek’s, Derek’s moving to thrust shallowly up into Stiles’, kissing the back of his neck.

And then Derek is tugging his shirt off and helping Stiles to do the same to his, and Stiles is leaning back against his ridiculous chest and lifting himself up enough that Derek gets the hint and starts sliding Stiles’ boxer briefs off before pushing his own down around his ankles.

Then they’re naked, like actual skin to skin contact, Stiles’ ass is _on_ Derek’s D finally. And there’s grinding, Derek’s hands tracing along Stiles’ chest and stomach, until he’s wrapping his hand around Stiles’ straining erection and jerking him off. Stiles’ already got a hair trigger and he knows he’s not going to last long.

Derek probably knows it too because he’s pushing at Stiles, trying to get him to turn around. He’s pretty mahandleable and then he’s settled on Derek’s lap, chest to chest, kissing each other, hands roaming over skin as they grind and hump. And then Derek gets his hands on both of them at once and that’s it, Stiles’ is done, and he tries to warn him but it all gets jumbled up in his throat like a three word pile up and he says “gocum” and then he’s coming and Derek is laughing until he’s not, and then he’s coming too and it’s just all jerking cocks and jizz everywhere and it’s fucking _awesome_ is what it is.

And then there’s some sappy desperate sort of clinging, Stiles staring into Derek’s eyes like he’s about to break out in a rounding chorus of a Whole New World. Instead they just sort of kiss and come down and Stiles doesn’t put his pants back on for the rest of the evening, and Derek doesn’t even mind.

 

After that, things sort of progress. Stiles sends Derek links to porn blogs and sex advice vlogs and they…fool around a lot more. The next time, Stiles gives Derek the sloppiest kind of blowjob he imagines it’s possible to give.  His dentist always tells him he has very active spit glands and he thinks he needs one of those spit sucker things for these occasions cos it’s fucking _everywhere_ , and he has almost no rhythm or anything but he also has like zero gag reflex so that’s something.

And then it’s Derek’s turn, and Stiles maybe noticed a few days earlier there were several empty boxes of popsicles in the recycling bin beneath Derek’s sink and at first he’d made kind of a joke about it to himself, but now he’s pretty convinced it wasn’t Derek’s sweet tooth and the steadily warming weather…

Because Derek is _good_ , like _good_ , like there are probably a lot of synonyms that are more appropriate but Stiles can’t think of anything so he just keeps petting Derek’s hair and saying ‘ _good_ ’ over and over. He thinks ordinarily Derek would be annoyed about it, because hello, dog joke in there somewhere, except Derek’s mouth is a little too busy to do things like snark.

He goes slow, like really slow, up and _down_ and then repeating over and over, one hand pressed against Stiles’ hips to keep him from budging an inch. And then he pulls off to kiss at Stiles’ dick, to nose along it and at his balls like he just wants to nuzzle it, maybe write poetry to it, spend the whole evening showering it in affection and emotional reassurance; and then getting back to sucking on it like it has a prize inside.

He varies his pace too, sometimes going so slow Stiles wants to smack him a little about the head but resists and then other times bobbing his head in quick little moves that has Stiles clutching at his shoulders, and grinding his ass down into the sheets of Derek’s bed beneath him and making ridiculous kinds of noises.

Stiles grabs at Derek’s head after a while and pulls him off, “isn’t your jaw sore?” He asks, a little awed. Derek just shrugs his shoulders and nods at him, “yeah, kinda?”

“Do you want to stop?” Stiles asks and Derek looks down at Stiles’ dick, hard as a rock, slick with spit and lying flush against his stomach.

“Not really?”

“Fuck yes,” Stiles agrees, pumping his fist half-heartedly in the air as Derek goes back down on him, “I love you,” he manages and then Derek swallows him to the back of his throat and returns the sentiment around his dick and Stiles _comes_.

 

Stiles knows that Derek is attracted to him, like obviously, and he’s also pretty comfortable with what he’s working with (he’s been naked in locker rooms enough to know by now he has nothing to be made fun of for in that department, blissfully), but he’s still awkwarded out by the thought of shoving some of his more private areas in Derek’s face, literally.

Derek on the other hand? He’s shy as fuck when it comes to his desire for things, but he’s also 100% comfortable in his own skin, which is a fascinating sort of counter intuitive quirk Stiles loves about him. So, when Stiles expresses his wish to try out rimming, Derek just sort of shrugs and says, “yeah, okay,” all nonchalant like he’s kind of indifferent, except they’re naked and he pops a pretty big boner at the _thought_ of it, so Stiles? He’s pretty excited.

He’s also even more excited when he finds out Derek fucking _prepped_ for it before Stiles’ arrival, and probably had done so each date night in anticipation for it. Derek starts off on his back, Stiles just pushes his legs up as he spreads them for him, and it’s the hottest fucking thing he’s ever seen or done, ever. Derek is sort of watching him with anticipation and Stiles is all enthusiastic nervous energy and he tries to say something sexy or stress relieving but he ends up just saying, “wow butthole” instead before he’s going for it like a heat seeking missile.

Stiles has many tired metaphors for the lavishing that he does at Derek Hale’s ass and they all pale in comparison to the way his face seems to be trying to break laws of quantum physics to get at more of it. Eventually, he flips Derek over on to his stomach, gets him on his hands and knees so he can spread his cheeks easier, thumb at his hole and stretch Derek open for his tongue.

Derek is making these ridiculous noises into his pillow, they’re all high pitched and breathy and he’s got this punch drunk look on his face like he can’t believe what’s happening back there. Eventually Stiles pulls off kind of dizzy with it, and asks, “could I like, finger you?” And Derek just nods and clutches at the bed a little harder and Stiles tries not to come in his pants. If he were wearing pants, which he is not, in fact, doing.

He gets three fingers into Derek’s ass, fucking him open slowly, before he does a little twisty thing and Derek _yelps_ out Stiles’ name and comes messily against the bed, ass clenching down tight around Stiles’ fingers.

“Oh wow, go me,” Stiles self congratulates while Derek just nods, legs still spread wide, lube dripping down the back of his balls. Afterwards, Stiles just stares at Derek’s loose and open hole and sticks his tongue back in, deep as it can go while Derek circles his hips back at him and sighs, satisfied.

“Do you want a turn?” Derek asks then, as he climbs into Stiles’ lap.

“Uh…maybe umm…maybe another night?” Stiles asks, flushing a little shyly.

“Want me to get you off?” Derek asks, nosing along Stiles’ throat, his eyes slip shut as Derek nibbles at the skin there. Stiles nods collapses back against the rumpled sheets and Derek smiles at him, kisses him deeply as he jerks him off instead, slips the tip of his finger to press teasingly against Stiles’ hole as he comes, clutching at Derek.

 

Maybe a week later Stiles plans a day trip three towns over to a sex shop to buy dildos in varying sizes. Derek stares at him in open disbelief and keeps his sunglasses on the whole time. “Do you want to see if they have fake moustaches too, or are you good?” Stiles teases. Derek scowls at him, “I can’t be seen buying sex toys with the Sheriff’s son.”

“We’re not even in Beacon Hills anymore, Derek.”

“Massachusetts would be too close to home to be seen buying dildos with you,” Derek argues. Derek flushes absolutely adorably when a cute petite blonde employee comes over to ask to see Stiles’ I.D and if they need any help finding anything. Stiles almost wants to torture Derek by dragging her around the store with them, but he politely declines her offer of help. Though before she leaves she points to various sections of the store, describes their contents.

“…and over there we have some of the more specialty toys—“

“Aren’t these _all_ specialty toys?” Derek asks.

“Well, those are for a more niche market, I think,” she explains, smirking a little.

“Ooh, like what?” Stiles asks, intrigued.

“Well, we’ve got vampire fleshjackets, zombie dildos,” Stiles and Derek make a face of equal horror, “werewolf dildos—“

“Whoa, wait what?” Stiles laughs. “What’s a werewolf dildo?”

“They’re a little bigger than most of the sizes we carry and they have knots,” she explains, and it’s all very nonchalant, like she’s describing sandwich selections and not lupine inspired sex toys.

“Knots?” Derek asks, and he’s scowling a little.

“Yeah, you know? Kind of like dogs and wolves have?”

“That’s really racist,” Derek huffs and Stiles tries not to laugh at the look of confusion on the woman’s face.

“Ah, thank you, I think we can take it from here,” Stiles laughs, tugging Derek in the opposite direction.

In the end they buy an eclectic variety of vibrators and dildos which Stiles pays for in cash while Derek lurks behind him, hovering in the edible underwear section like a creeper.  

 

It’s about a month and a half after that first initial conversation before they finally do it, the _sex_.

“I will literally never have sex with you if you don’t stop calling it that, Stiles,” Derek tries to threaten, but Stiles just shakes his head.

“We’re totally gonna do the sex tonight, Derek, you promised,” Stiles informs him, “don’t make a liar of yourself.”

“Stiles-“

“Wait shh shh hold on,” Stiles hushes him, scrolls through his ipod and plugs it into the speakers he’s set up on Derek’s dresser.

“… _And I can feel it coming in the air tonight_ ,” the musical stylings of Phil Collins wafts out as Stiles saunters dramatically over to the bed, lip synching. Derek is staring at Stiles incredulously.

“Oh my G—“ but Stiles presses his  index finger to Derek’s lips a little off center, smooshing them shut.

“Don’t ruin this for me,” he chastises quickly before belting out, “AND I’VE BEEN WAITING FOR THIS MOMENT, FOR ALL MY LIFE!”

“Stiles!” Derek bats his hand away, grabs him around the wrist and manhandles him onto the bed while Stiles laughs happily, Derek smiling fondly down at him in spite of himself. They kiss for a long while until Derek pulls back and asks, “do you want to?”

“No, Derek, we’ve both been fucking each other with dildos for the last two weeks for our _health_ ,” Stiles snarks. Because they’ve both been prepped and readied for this, willing to go either way on the whole switch pitch game, but here and now Stiles is fingering the collar of Derek’s shirt and saying, “I want you to fuck me,” and Derek looks down at him with equal measures of excitement and trepidation.

And then there’s foreplay, which up until now has been pretty satisfying for Stiles, because it’s mostly been less fore and more just play. But now, Stiles is being slowly driven up the padded wall because he’s fucking _crazy_ with need and want and the insatiable desire for Derek to be, “fucking in me _like now_.”

And then he is, all lubed up and hard and pushing so slow and careful against Stiles’ loosened hole. Stiles has been fucked with toys nearly equal to Derek’s girth and length so it doesn’t really hurt but it’s _different_. Cos it’s _Derek_. It’s fucking Derek inside him, making those faces because of _him_ , because of his ass clenching tight around him.

“Oh holy God,” Stiles nods, clutching at Derek’s biceps, legs wrapped loose around his middle as Derek starts to fuck him, watching him like he can’t take his eyes off the way Stiles is saying his name over and over. Stiles is trying to help fuck himself against Derek’s cock, but mostly he’s just clinging to Derek, to the headboard, to the sheets around him trying not to fall off the Earth while Derek’s hips snap against his. Derek seems pretty okay with the arrangement though, slamming up into Stiles and pulling him back against him, Stiles splayed out on his back on the bed.

It doesn’t take long before Stiles feels his orgasm build, he grabs his cock and balls, plays with himself sloppily as Derek fucks him a few more times and then Stiles is coming against his stomach, crying out with it, arching up into Derek.

Derek envelopes Stiles then, like he’s trying really hard to merge them into one collective being, and his hips snap against Stiles’ once more before he’s stilling, and Stiles can _feel_ him coming, can feel him pulsing inside him and, “holy shit, Derek!”

“Oh fuck, Stiles,” Derek groans against his ear and Stiles wishes they’d like recorded this for posterity. Cos when he’s old and senile and forgets these things he wants like a record, like a hardcopy record of this moment, the moment Derek Hale came in his ass because he’s pretty sure Siddhartha never even managed to reach this level of Nirvana.

“Fuck you do good in the bed,” Stiles nods, and he pats Derek’s slumped form on the back happily.

“You are equally gifted at the sex,” Derek agrees, and Stiles laughs so hard he dislodges Derek’s cock from his ass, Derek burying his face in Stiles’ neck and holding on.

 

 

 

 

 


End file.
